Tag: 100-200

《Drug-like biimidazole derivatives dually target c-MYC/BCL-2 G-quadruplexes and inhibit acute myeloid leukemia》 was published in Bioorganic Chemistry in 2020. These research results belong to Hu, Ming-Hao; Yu, Bing-Ying; Wang, Xiaodong; Jin, Guangyi. Formula: C5H12N2 The article mentions the following:

Chemotherapy is the main approach for treating acute myeloid leukemia (AML). However, this therapy can cause severe side effects as well as drug resistance, hence calling for new therapeutic strategies. As c-MYC and BCL-2 are often overexpressed in AML, and synergism between c-MYC and BCL-2 promotes tumorigenesis, therefore, dual targeting of c-MYC/BCL-2 promoter G-quadruplexes (G4s) and then inhibiting the targeted gene expression would be a potential strategy in ALM treatment. In this work, in the search of dual ligands, we performed a screening assay with an inhouse, imidazole-based compound library. Consequently, two drug-like biimidazole derivatives were identified as selective c-MYC/BCL-2 G4 binders, of which, BIM-2 was selected as the candidate for inhibiting AML cell growth. Then, BIM-2 was demonstrated to downregulate both c-MYC and BCL-2 expression, and thereby cause cell cycle arrest at G0/G1 phase and apoptosis in AML cells. Furthermore, the possible end-stacking binding modes between BIM-2 and c-MYC/BCL-2 G4s were revealed by NMR and mol. docking studies. Accordingly, this study provides a new class of drug-like dual-selective c-MYC/BCL-2 G4 ligands for the potential treatment of AML. In the part of experimental materials, we found many familiar compounds, such as 1-Methylpiperazine(cas: 109-01-3Formula: C5H12N2)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Formula: C5H12N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The author of 《Development of a FRET-based ratiometric fluorescent probe to monitor the changes in palladium(II) in aqueous solution and living cells》 were Wang, Li; Ren, Mingguang; Li, Zihong; Dai, Lixuan; Lin, Weiying. And the article was published in New Journal of Chemistry in 2019. Formula: C5H12N2 The author mentioned the following in the article:

The enrichment of palladium ions in organisms can harm organisms to a great extent. It is necessary and critical to develop mol. tools that can ratiometrically image Pd2+ in living cells. Herein, we have developed a new FRET-based ratiometric fluorescent probe (CR-Pd, I) for the specific determination of Pd2+ in living cells. Moreover, fluorescence imaging shows that CR-Pd could be used as a probe for the ratiometric visualization of Pd2+ in mitochondria. The results came from multiple reactions, including the reaction of 1-Methylpiperazine(cas: 109-01-3Formula: C5H12N2)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Formula: C5H12N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《Synthesis, characterization, and in vivo pharmacological evaluation of novel Mannich bases derived from 1,2,4-triazole containing a naproxen moiety》 was written by Avci, Ahmet; Tasci, Hayrunnisa; Kandemir, Ummuhan; Can, Ozgur Devrim; Gokhan-Kelekci, Nesrin; Tozkoparan, Birsen. Synthetic Route of C5H12N2This research focused ontriazolethione regioselective preparation antinociceptive antiinflammatory mol docking; methoxynaphthylethylmercaptotriazole piperazine Mannich reaction; 1,2,4-Triazole-5-thione N-Mannich derivatives; Anti-inflammatory activity; Antinociceptive activity; Gastric toxicity; Mannich reaction; Naproxen analogs. The article conveys some information:

A new series of 1,2,4-triazole-5-thione Mannich derivatives I (R = Me, 4-fluorophenyl, 4-pyridyl, etc.) containing a naproxen moiety was designed and synthesized to create naproxen analogs, with the aim of developing novel anti-inflammatory/analgesic agents with improved safety profiles. Target compounds were synthesized using classical Mannich reaction (i.e. one-pot three component condensation reaction), by reacting 3-[1-(6-methoxy-2-naphtyl)ethyl]-5-mercapto-1,2,4-triazole, formaldehyde, and diverse secondary amines II in ethanol. Compounds were then evaluated for their potential antinociceptive and anti-inflammatory activities using some validated in vivo methods. Data obtained from acetic acid induced-writhing and carrageenan-induced paw edema tests revealed that all compounds induced peripherally-mediated antinociceptive activities, as well as notable anti-inflammatory effects. The results of hot-plate and tail-clip tests indicated that compounds I (R = Me, Et, 2-fluorophenyl, 4-fluorophenyl, 4-methylphenyl, 4-acetylphenyl) have also centrally-mediated antinociceptive activities in addition to their peripherally-mediated effects. Mol. docking studies were performed to investigate the putative binding modes of the interactions between all compounds and COX-1/COX-2 enzymes using AutoDock Vina software. Docking of the compounds into the COX-2 active site produced binding interactions that are essential for COX-2 inhibitory activity. None of the compounds in the serial, except for I (R = Boc and 4-acetylphenyl), induced significant gastrointestinal irritation. Overall, the results indicated that triazole Mannich bases bearing a naproxen moiety potentially represent a novel class of antinociceptive and anti-inflammatory agent with an improved gastric safety profile. In the experiment, the researchers used many compounds, for example, 1-Methylpiperazine(cas: 109-01-3Synthetic Route of C5H12N2)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Synthetic Route of C5H12N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《Design and synthesis of quinoxaline-1,3,4-oxadiazole hybrid derivatives as potent inhibitors of the anti-apoptotic Bcl-2 protein》 was written by Ono, Yukari; Ninomiya, Masayuki; Kaneko, Daiki; Sonawane, Amol D.; Udagawa, Taro; Tanaka, Kaori; Nishina, Atsuyoshi; Koketsu, Mamoru. Quality Control of 1-Methylpiperazine And the article was included in Bioorganic Chemistry in 2020. The article conveys some information:

A series of quinoxaline-1,3,4-oxadiazole hybrids I [R = chloro, Ph, 4-methylpiperazin-1-yl, 4-phenylpiperazin-1-yl, etc.; R1 = hydroxy, amino, 2-phenylethoxy, etc.] were synthesized and assessed for their anticancer potential on human leukemia HL-60 cells. Although these hybrids I exerted significant inhibition of HL-60 cell proliferation, they showed high cytotoxicity on human normal cells (WI-38). Utilizing information from mol. modeling of the hybrids I to the anti-apoptotic Bcl-2 protein, substructures including Ph, piperazine, piperidine and morpholine rings were added to their frameworks. The designed compounds I successfully induced apoptotic response on HL-60 cells with low toxicity on WI-38 cells. Furthermore, RT-PCR anal. demonstrated that these compounds I predominantly inhibited Bcl-2 expression. These findings highlight the great potential for the development of synthetic quinoxaline-1,3,4-oxadiazole hybrid derivatives as proapoptotic anticancer agents. In the experiment, the researchers used 1-Methylpiperazine(cas: 109-01-3Quality Control of 1-Methylpiperazine)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Quality Control of 1-Methylpiperazine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The author of 《Anion exchange membranes with “”rigid-side-chain”” symmetric piperazinium structures for fuel cell exceeding 1.2 W cm-2 at 60°C》 were Gao, Li; Wang, Ying; Cui, Chunyu; Zheng, Wenji; Yan, Xiaoming; Zhang, Peng; Hu, Lei; Wu, Xuemei; Zhuang, Lin; He, Gaohong. And the article was published in Journal of Power Sources in 2019. Category: piperazines The author mentioned the following in the article:

Developing anion exchange membranes (AEMs) having high hydroxide conductivity, swelling resistance and excellent alk. stability is a challenge for fuel cells now. Herein, a universal and controllable approach of grafting rigid side chain is first proposed to construct connected ion transport nano-channels. A new route is also provided to prepare AEMs with stable sym. saturated heterocyclic ammonium. The rigid side chain is introduced onto poly(2,6-dimethyl-1,4-phenylene oxide) (PPO) by the Friedel-Crafts acylation with 4-fluorobenzoyl chloride and subsequent reaction between Ph fluoride and secondary amine of 1-methylpiperazine. Then the terminal piperazinium is produced by the reaction between tertiary amine of 1-methylpiperazine and Me iodide. Rigid branches expand free volume to construct connected ion transport nano-channels, leading to excellent conductivity (108 mS cm-1 at 60°C) that is higher than those of other reported sym. heterocyclic ammonium functionalized AEMs (33-89 mS cm-1 at 60°C). Due to the high conductivity, the H2/O2 cell employing this membrane achieves one of the highest peak power densities (1210 mW cm-2 at 2600 mA cm-2) so far. In addition, the IEC of the membrane remains constant after testing in 1 M NaOH at 60°C over 500 h.1-Methylpiperazine(cas: 109-01-3Category: piperazines) was used in this study.

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Category: piperazines

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The author of 《Antimicrotubular activity of 2-(4-methyl-1-piperazinylmethyl)acrylophenone dihydrochloride》 were Lesieur, I.; Delacourte, A.; Cazin, M.. And the article was published in Acta Therapeutica in 1984. Application In Synthesis of 1-Methylpiperazine dihydrochloride The author mentioned the following in the article:

The antimicrotubular activity of 3-(4-methyl-1-piperazinyl)propiophenone (I) [60868-01-1] was due to contamination of the synthetic product with 2-(4-methyl-1-piperazinylmethyl)acrylophenone (II) [91401-12-6]. Synthesis of I-2HCl [5470-92-8] and II-2HCl [91401-13-7] is described. Whereas I was devoid of any antimicrotubular activity, II, although less potent than colchicine, showed antimicrotubular activity. In addition to this study using 1-Methylpiperazine dihydrochloride, there are many other studies that have used 1-Methylpiperazine dihydrochloride(cas: 34352-59-5Application In Synthesis of 1-Methylpiperazine dihydrochloride) was used in this study.

1-Methylpiperazine dihydrochloride(cas: 34352-59-5) is used in the preparation of 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), 1-methylpiperazine-1,4-diium tetrachloridozincate hemihydrate, 2-(4-Methyl-1-piperazinylmethyl)acrylophenone(MPMAP), an antimicrotubular drug..Application In Synthesis of 1-Methylpiperazine dihydrochloride

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Computed Properties of C5H11ClN2O2SOn October 12, 2017 ,《Discovery of Novel Macrocyclic Hedgehog Pathway Inhibitors Acting by Suppressing the Gli-Mediated Transcription》 was published in Journal of Medicinal Chemistry. The article was written by Liu, Gang; Huang, Wenjing; Wang, Juan; Liu, Xiaohua; Yang, Jun; Zhang, Yu; Geng, Yong; Tan, Wenfu; Zhang, Ao. The article contains the following contents:

A systemic medicinal chem. campaign was conducted based on a literature hit compound I bearing the 4,5-dihydro-2H-benzo[b][1,5]oxazocin-6(3H)-one core through cyclization of two side substituents of the bicyclic skeleton combined with N-atom walking or ring walking and the central ring expansion or extraction approaches, leading to several series of structurally unique tricyclic compounds Among these, compound II was identified as the most potent against the Hedgehog (Hh) signaling pathway showing an IC50 value of 23 nM. Mechanism studies indicated that compound II inhibited the Hh signaling pathway by suppressing the expression of the transcriptional factors Gli rather than by interrupting the binding of Gli with DNA. We further observed that II was equally potent against both Smo wild type and the two major resistant mutants (Smo D473H and Smo W535L). It potently inhibited the proliferation of medulloblastoma cells and showed significant tumor growth inhibition in the ptch± ;p53-/- medulloblastoma allograft mice model. Though more studies are needed to clarify the precise interaction pattern of II with Gli, its promising in vitro and in vivo properties encourage further profiling as a new-generation Hh signaling inhibitor to treat tumors primarily or secondarily resistant to current Smo inhibitors. In the experimental materials used by the author, we found 4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5Computed Properties of C5H11ClN2O2S)

4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.Computed Properties of C5H11ClN2O2S

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《Optimization of phthalazin-based aryl/heteroarylhydrazones to design new promising antileishmanicidal agents: synthesis and biological evaluation of 3-aryl-6-piperazin-1,2,4-triazolo[3,4-a]phthalazines》 was written by Romero, Angel H.; Rodriguez, Noris; Ramirez, Oscar G.. Computed Properties of C5H12N2 And the article was included in New Journal of Chemistry in 2020. The article conveys some information:

1-Monosubstituted and 1,4-substituted phthalazins based on aryl/heteroarylhydrazinyl have demonstrated attractive antileishmanial profiles against amastigote forms of the Leishmania braziliensis parasite. Further optimization of the mentioned acyclic scaffold motivated us to design a series of 3-aryl-1,2,4-triazolo[3,4-a]phthalazines, cyclic versions of the phthalazins based on aryl/heteroarylhydrazinyl, which have not been evaluated against Leishmania parasites yet. In order to compare to phthalazine-based aryl/heteroarylhydrazones, five essential 3-aryl-6-piperazin-1,2,4-triazolo[3,4-a]phthalazines were efficiently prepared in excellent yields (73-83%) through a facile one-pot procedure from 4-chloro-1-phthalazinyl-arylhydrazones via C-H dehydrogenative cyclization using silver(I) salt. From in vitro antileismanial evaluation, compound 2d, a nitro derivative, was identified as the most promising agent with a good anti-amastigote response (IC50 = 9.37 μM) and low relative toxicity against peritoneal macrophages (LD50 = 123.93 μM). A moderate response was found against clin. amastigote isolates of L. braziliensis, although superior compared to the reference glucantime. A comparison with their phthalazin analogs based on aryl/heteroarylhydrazinyl gave evidence that the efficacy of each chem. system is determined by the nature of the functionalization next to the aryl moiety, which suggests that different mechanisms of action are involved for each chem. system. The cyclized form led to an enhancement of the antileismanial activity compared to the acyclic form, but the nitroderivatives seemed to be highly more toxic than the parent non-cyclized compounds From the three compared phthalazine groups, 4-chloro-1-phthalazine-(5-nitrofuryl)hydrazinil with a nanomolar antileishmanial response was identified as a promising lead for further optimization, whereas compound 2d emerges as a prominent hit platform to prepare a group of derivatives based on phthalazine-1,2,4-triazolo bearing 3-nitro-Ph at the 3-position. The results came from multiple reactions, including the reaction of 1-Methylpiperazine(cas: 109-01-3Computed Properties of C5H12N2)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Computed Properties of C5H12N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

In 2019,Organic Chemistry Frontiers included an article by Zhang, Fei-Yi; Lan, Xiao-Bing; Xu, Chang; Yao, Hua-Gang; Li, Tian; Liu, Feng-Shou. Formula: C5H12N2. The article was titled 《Rigid hindered N-heterocyclic carbene palladium precatalysts: synthesis, characterization and catalytic amination》. The information in the text is summarized as follows:

To explore the high efficiency of the Buchwald-Hartwig amination with a wide substrate scope, easily prepared and air stable palladium precatalysts bearing rigid hindered N-heterocyclic carbenes (NHCs) were synthesized and characterized. A simple and efficient protocol for the amination of (hetero)aryl chlorides with amines is described, which revealed that sterically encumbered NHC ligands are crucial to promote the transformation. It is highlighted that the most challenging reactions could be performed between less reactive five-membered heteroaryl chlorides and heteroanilines. This methodol. provides a rapid and straightforward access to a wide range of arylated amines with excellent functional group tolerance. Remarkably, the powerful synthetic utility of palladium precatalysts was further extended to the synthesis of pharmaceuticals. After reading the article, we found that the author used 1-Methylpiperazine(cas: 109-01-3Formula: C5H12N2)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Formula: C5H12N2

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《Microwave-Assisted Cu(I)-Catalyzed Synthesis of Unsymmetrical 1,4-Diamino-2-butynes via Cross-A3-Coupling/Decarboxylative A3-Coupling》 was written by Xu, Xianjun; Feng, Huangdi; Van der Eycken, Erik V.. Safety of 1-MethylpiperazineThis research focused onunsym diamino butyne preparation chemoselective microwave irradiation; amine formaldehyde propiolic acid decarboxylative cross coupling copper. The article conveys some information:

1,4-Diamino-2-butynes display both chem. and physiol. properties. Here a highly efficient synthesis avenue to generate unsym. 1,4-diamino-2-butynes has been developed by microwave-assisted Cu(I)-catalyzed cross-A3-coupling/decarboxylative coupling of two different amines, formaldehyde, and propiolic acid through a domino process. This multicomponent reaction provides a series of target products in moderate to good yields with high chemoselectivity. In the experiment, the researchers used many compounds, for example, 1-Methylpiperazine(cas: 109-01-3Safety of 1-Methylpiperazine)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Safety of 1-Methylpiperazine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics